


One Night Stand

by abitofarockyroad



Category: Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2014-09-15
Updated: 2014-09-15
Packaged: 2018-02-17 12:14:47
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,732
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2309300
Author URL: https://archiveofourown.org/users/abitofarockyroad/pseuds/abitofarockyroad
Summary: <blockquote class="userstuff">
              <p>A one night stand AU before the first day of your new job and oops it was your boss you were sleeping with</p>
            </blockquote>





	One Night Stand

**Author's Note:**

> Sorry for the delay but this one turned out rather unintentionally long xD I can’t seem to regulate the lengths of my oneshots… I switched this one around slightly so the reader is the boss. Hopefully you’ll understand the comic value of this once you’re finished reading xD - Bella xxx

You walked into the bar slightly cautiously. Drinking in this kind of place wasn’t generally your kind of thing. Curling up next to a fire with a glass of wine and a good book was more your style. However, it was your best friends birthday so you made an exception.

"(Y/N)!!!" You hear shouted across the bar. You spin blindly, trying to locate the direction from which the shout had come from. It wasn’t long though before you saw a head of curly blonde hair bouncing towards you.

"Hey Jess." You say with a grin, pulling her into a tight hug when she has successfully woven through all the bodies to reach you.

"Oh god I’ve missed you so much!"

"I know I’ve missed you too. I’m big boss at the company now and it is ridiculous how many shit heads are allowed to work at the fucking place. I had to explain to some temp how to use a fucking stapler today, I kid you not." You explain.

"Good to see your levels of sarcasm are as high as ever." Jess comments thoughtfully, before breaking into a huge grin.

"Would you expect anything less?"

"From you? Never. Shall we get a table?" Jess asks, peering round people to get a glimpse at the tables lining the bar. It was classier than you had first thought. There was minimal grinding and twerking at least which you could only take as a good thing.

"There’s one." You exclaim, pointing at the four seated table that had opened up. The pair of you walk towards it quickly and throw yourselves into the seats before anyone else can.

"So who else are we waiting for?" You ask, kicking off your heels. You were forced to come out and you were determined you’d be at least mildly comfortable.

"Nobody. Just us." Jess answers with a grin.

"Jess its your birthday! Why isn’t anyone else coming?!" you ask, genuinely shocked.

"I didn’t invite anyone else."

"You what now?"

"(y/n) you’re my best friend, I haven’t seen you in ages and you’re the only person I want to be with on my birthday. If other people were here I wouldn’t be able to talk to you." Jess explains, smiling at the look of surprise on your face.

“Well then.” You say, momentarily lost for words. “Let’s get wasted.”

“I was hoping you’d say that.” Jess says with a grin, waving over the barman.

2 hours later you and Jess were at that stage where you were slowly moving from tipsy to drunk.

“I…am important.” You say, thinking carefully about your words. “I have a big job. Big. Why can I not find a nice guy to be nice to me? Nice?” You say, taking another sip of your drink. Jess looks at you carefully before answering.

“I don’t know…” Is all she offers as a reply. Just as she goes to have another sip of drink, her mouth falls open. “Speaking of guys. Check out the two hot pieces of ass that just walked in.”

“I do like a good hot piece of ass.” You mutter as you spin round in your chair to face the doorway.

“Daym…” Jess murmurs as you look both guys up and down, taking in everything. There was the tall one. His floppy brown hair was just long enough to flutter in a breeze, but didn’t fall into his eyes. You could tell even through his slightly puffy jacket that he had hella muscles. Your eyes however are drawn to the shorter of the two. You start at his feet, noting the scuffed but clearly loves DMs, moving to the ripped and over worn jeans, then the tshirt that wasn’t tight enough that it gave anything away, but was tight enough to just tease you, the leather jacket that make his arm muscles nicely defined. Then the jaw, the green eyes, the hair just long enough you could quite successfully run your fingers through it and have a good grip.

“Dibs on the tall one.” Jess whispers in your ear.

“Deal.” You reply immediately.

“God damn…those are faces made for sitting on.” Jess says with a smirk as you turn back in your seat to face her. You snort into your drink at the downright dirty look on your friends face. This dirty look quickly turns to panic.

“What?” You ask quickly.

“They’re walking in this direction.”

“And?” You ask patiently.

“What do we do?!”

“We try not to act like complete and utter psychopaths.” You say.

“Complete and utter psychopaths? They’re my favourite kind.” You hear from behind you in a gorgeously husky voice. You turn slowly to see the shorter guy smiling down at you.

“Oh really? Well then you’re in the right place my friend. Please, do have a seat.” You say with a smirk, gesturing at the two empty seats at your table. The taller guy scrambles around the table and practically jumps into the seat next to Jess.

“Smooth.” You and the smaller guy say under your breath simultaneously. At this he chuckles and sits next to you, holding out his hand.

“The names Dean.” He says formally, shaking your hand firmly as you take his. “This is my brother Sam.”

“I’m (y/n).” You reply, waiting for Jess to share her name. However she seems to busy staring at Sam to even notice she’s part of the conversation. You wouldn’t be surprised if she started drooling soon. “And that’s Jess.”

At the mention of her name, Jess seems to snap out of her trance. “Yes?”

“No dear. I was introducing you to Sam and Dean.” You explain, with only a hint of your normal sarcasm tinting your voice.

“Oh…right.” She says absently, returning to staring at Sam who doesn’t seem to mind in the slightest.

“Well then. This rounds on me. (y/n), gimme a hand?” Dean says, standing up. You nod and stand, following him to the bar.

“How much are you willing to bet me that those two start making out in the next 10 minutes?” You say once you’re out of earshot.

“I’d say an hour honestly. Sammy doesn’t have much game when it comes to women.” Dean says thoughtfully. You pull out your purse and look inside.

“I bet you….$45.60.” You say, counting all the money you have with you.

“You’re on.” Dean replies with a grin, shaking your hand to seal the bet.

“So how do you know Sam?” You ask after Dean orders 4 beers.

“He’s my baby brother.” Dean explains. “We stayed pretty close. With the way our family was I was essentially the only person he had to look after him. What about you and Jess?”

“We went to college together. Both in the same dorms first year, got a flat together for the other two and we stayed flat mates for quite a while after that. I had to move out though. I got promoted and got a new flat simply for convenience with travel, but she stayed here for work. I’m back today for her birthday.”

“Ah ok. College eh? Sororities?” Dean asks with a cheeky grin on his face.

“Ah yes. You would not believe the amount of naked pillow fights we had. After a couple of years they did get slightly boring.” You say. Dean’s mouth falls open and his eyes widen in shock.

“You…pillow…naked…” He stammers.

“Oh shut your mouth Dean, we are not a codfish.” You say in a mock British accent, before sighing at Dean’s blank expression. “Mary Poppins? Come on. No?”

“What the hell are you on about…?”

“Never mind. No we didn’t have naked pillow fights. But you owe me $45.60.” You say, when you turn around to look at Sam and Jess.

“What?!” Dean gasps, spinning round to see Sam and Jess furiously making out, Jess practically straddling Sam.

“Sam might not have game, but Jess does.” You say, almost proud of your friend. She had just earned you almost $50.

“Well. You’re not wrong.” Dean says, shaking his head despairingly as he hands you the cash.

“Thank you.” You say smugly, tucking it straight into your bra. “If you’re lucky you might just get to take that out later.” You say, grabbing two beers, winking at Dean and walking back over to your table. You glance back at Dean over your shoulder and see him watching you walk, his eyes roaming your body and a genuine smile on his face.

“Beer.” You say when you reach the table, Dean arriving shortly after you. When Sam and Jess don’t acknowledge you, you try again. “BEER.” You practically shout, making the pair jump apart from each other.

“Hello everyone this report is coming to you live from ‘The Bar’ where we have come across Sam and Jess. We have Sam’s brother here to speak with us. Dean, how do you feel about this sudden turn of events?” You say, using your beer bottle as a microphone. You hold it out to Dean as if interviewing him. He looks shocked for a couple of seconds, but quickly catches up and goes with it.

“Well (y/n), I’m shocked. Sammy, my darling brother, isn’t generally one to woo the ladies. Yet look what we have tonight.”

“I agree Dean. I agree. Well more on this wondrous anomaly after the weather. Back to you Chris.” You say, turning and staring into space.

“(y/n)?” Jess asks, laughing.

“Yeah I need to stop drinking…” You say slowly, staring at your beer as you and Dean sit back down.

“Well…me and Jess are going to…urmm…we are gunna…”

“You kids go have fun. Bang like there’s no tomorrow.” You say, enjoying watching the pair of them squirm. Dean reaches into his pocket and flicks Dean a motel room card.

“Where are you going to sleep?” Sam asks, picking up the card.

“Oh I can think of somewhere.” You answer, suddenly feeling ridiculously brave.

“Alright then.” Sam says, clearly feeling quite awkward. As him and Jess stand up, you follow.

“You coming?” You ask Dean, stopping and turning back to him as you make your way to the door.

“Oh fuck yes.” He says and bounds after you, walking in front of you to hold the door open.

“Well how chivalrous.” You say, curtsying. Dean bows, then holds out his arm. You take it and let him escort you to his car. Sam and Jess had already disappeared off in Jess’ car, leaving you and Dean alone in the dark car park. Dean’s arm unhooks from yours when he digs into his jean pocket to retrieve his car keys. When he locates them, you feel his hand snake around your waist and slowly move up.

“Dean are you trying to feel me up in this dark secluded car park?” You ask, feeling the hand instantly move back to your waist.

“Well that wouldn’t be very chivalrous of me would it?” He says, removing his arm to open the car door for you. You slide in and try to relax, letting the feeling of panic shrink as you give Dean directions to your flat.

—-The Next Day—-

You walk into your office, trying not to think too hard about how you’d woken up this morning to a scrap of paper instead of Dean.

(y/n), I’m sorry I left before you woke up. I’ve got a job interview today, I figured I should go home and change before I turned up in a shirt soaked with many different liquids. I’ll call you xx

Sitting in your desk, you put the note in your drawer and sigh. Your diary is opened in front of you, and you scan it quickly. First thing was a meeting with a possible new mechanic. You didn’t even realise any mechanics worked at this damn company. It’s a big company. The appointment is at 10am, and its 9:55am now. You don’t even have time to go get a coffee.

*There’s a Mr Winchester here to see you about the mechanic job (y/n)* You hear over your intercom.

“Thanks Debbie. Send him straight in.” You reply. You put your head in your hands and rub your temples, massaging the headache that had slowly been increasing all morning. Damn alcohol. You hear the door open and force a smile on your face as you look up.

“Hello Mr Winches…oh fuck me.” You say in complete shock as Dean walks into the room. He freezes and stares when he sees you sitting behind your desk.

“Well then…” He says, standing awkwardly.

“Sit down.” You sigh, waving at the chairs in front of your desk. He sits down and hesitantly places his resume on your desk.

“You could have told me you were head of a company.” He says after a few minutes of silence.

“Well it didn’t really come up now did it.” You say in exasperation. “Right. Time for your interview.”

“Seriously? You’re still going to interview me?” He asks incredulously.

“Well that’s ma job Deany boy.” You say, sarcasm practically dripping off your words onto the floor.

“Alright. Go ahead.” He replies, getting comfortable in the chair.

“So. Dean. The hours will be quite…long and hard.” You say, letting your voice turn silky and seductive. He clearly notices and his eyes snap to yours. You can see him visibly gulp before he replies.

“I think I can ur…manage it.”

“It’s going to be rough. Do you like it nice and rough Dean?” You ask, leaning forward in your chair. When he doesn’t reply you continue.

“I can imagine it would get very hot and sweaty. Clothes sticking to skin.”

“Why do this?” Dean gasps, shifting in his seat awkwardly.

“It amuses me.” You say with a shrug, smiling at the difficult situation Dean is in. “Got yourself a small problem there do we?”

“Not that small.” Dean scoffs.

“Did you want me to add that to your resume?” You ask with a smirk. Dean glares at you from the chair, but then stands up. He moves his way round your desk and towards your chair.

“What are you…” You gasp as Dean pulls you out of your chair, sits himself down then pulls you onto his lap so you’re straddling him. His lips force themselves onto yours, stopping any thought of finishing your sentence. You melt into the kiss, moulding against his body as you attempt to get as close as possible to him.

“Someone could walk in.” You breathe into the kiss.

“I don’t care.” Dean murmurs back, one of his hands knotted into your hair, the other exploring your body.

“Come on. Stop.” You say, only half-heartedly trying to get off his lap. After a few more minutes of intense kissing, there is a knock on your door. You jump off Dean and he sprints round to sit back in the chair opposite you. You flatten your hair and do up the buttons of your blouse Dean had somehow managed to undo with one hand.

“Come in.” You call. The door opens revealing your assistant Debbie and a man you didn’t know.

“Your intercom wasn’t working.” Debbie says with a very pointed look that told you she knew exactly what had been going on. “This is Bobby, he wants to know if you’ve hired his new mechanic yet.”

“Give me a minute, I’m just finishing off the interview.” You say, dismissing the pair. They shut the door and Dean grins.

“Well I slept with the boss so I figure I deserve the job.” He says cheekily.

“Fuck it. Fine. If you screw up I have to answer for it though. Now get out. Go make friends with whoever Bobby is.” You sigh.

“What time do you finish today?” Dean asks as he walks towards your door.

“Probably about 7. Why?”

“I’ll pick you up outside?” He says, his hand now on the door handle.

“Ok.” You say with a nod, and try not to laugh as he beams at you like a child at Christmas before opening the door and walking out, shutting it behind him.

“Dear god what have I gotten into.” You mutter to yourself, picking up your phone to call Jess and tell her every single detail of what had just happened.

**Author's Note:**

> Hope you enjoyed it :) Check out our tumblr abitofarockyroad.tumblr.com for more of our stuff xx


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